US20060252874A1 - Thermoplastic elastomer composition with an improved rubber pelletization process - Google Patents

Thermoplastic elastomer composition with an improved rubber pelletization process Download PDF

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Publication number
US20060252874A1
US20060252874A1 US10/548,063 US54806303A US2006252874A1 US 20060252874 A1 US20060252874 A1 US 20060252874A1 US 54806303 A US54806303 A US 54806303A US 2006252874 A1 US2006252874 A1 US 2006252874A1
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US
United States
Prior art keywords
nylon
antioxidant
thermoplastic elastomer
elastomer composition
elastomer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US10/548,063
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English (en)
Inventor
Yoshihiro Soeda
Andy Tsou
Joyce Caraway
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Yokohama Rubber Co Ltd
ExxonMobil Chemical Patents Inc
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Individual
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Assigned to EXXONMOBIL CHEMICAL PATENTS, INC., THE YOKOHAMA RUBBER CO., LTD. reassignment EXXONMOBIL CHEMICAL PATENTS, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SOEDA, YOSHIHIRO, TSOU, ANDY H., CARAWAY, JOYCE F.
Publication of US20060252874A1 publication Critical patent/US20060252874A1/en
Priority to US11/932,651 priority Critical patent/US20080058472A1/en
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
    • C08L23/28—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment by reaction with halogens or compounds containing halogen
    • C08L23/283—Halogenated homo- or copolymers of iso-olefins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2312/00—Crosslinking

Definitions

  • the present invention provides an improved thermoplastic elastomer composition having excellent durability, heat resistance and flexibility, while possessing superior air impermeability.
  • the present invention relates to a thermoplastic elastomer composition using an antioxidant as an anti-blocking agent, where the antioxidant used has a melting temperature more than 70° C. and less than 200° C.
  • EP722850B1 disclosed a low-permeability thermoplastic elastomer composition that is superior as a gas-barrier layer in pneumatic tires.
  • This thermoplastic composition comprises a low-permeability thermoplastic matrix, such as polyamides or blends of polyamides, in which a low-permeability rubber such as brominated poly(isobutylene-co-p-methylstyrene) (i.e., BIMS) is dispersed.
  • BIMS brominated poly(isobutylene-co-p-methylstyrene)
  • Viscosity ratio between the thermoplastic matrix and the rubber dispersion was specified as a function of the volume fraction ratio and independently to be close to one in order to achieve phase continuity in thermoplastic and fine rubber dispersions, respectively.
  • Criticality of smaller rubber dispersions was recognized in EP969039A1 in these thermoplastic elastomers for delivering acceptable durability especially for their usage as innerliners in pneumatic tires.
  • the object of the present invention is to provide a thermoplastic elastomer composition having an improved durability, heat resistance and flexibility, while possessing superior air impermeability.
  • thermoplastic elastomer composition having improved durability, heat resistant and flexibility comprising a dynamically vulcanized blend of (A) a halogenated isobutylene elastomer, (B) polyamide and (C) an antioxidant having a melting temperature more than 70° C. and less than 200° C., wherein the elastomer (A) is dispersed as a domain in a continuous phase of the component (B) and the components (A) and (B) are dynamically vulcanized in the presence of the antioxidant as an anti-blocking agent.
  • the present invention relates to a thermoplastic elastomer composition, more particularly relates to a thermoplastic elastomer composition excellent in durability and in impermeability.
  • This thermoplastic elastomer contains rubber particles with improved rubber pelletization process. More specifically, rubber compounds are pelletized with the usage of antioxidants as the anti-blocking agent where antioxidants used having a melting temperature more than 70° C. and less than 200° C.
  • the rubber compounds and polyamides are dynamically vulcanized in the presence of an antioxidant such as triphosphite antioxidants, hindered phenol antioxidants either alone or in the combination with other antioxidant(s), at preferably 5 phr (i.e., parts by weight per hundred rubber) or less, more preferably 4 phr or less, still more preferably 3 phr or less, further more preferably 2 phr or less, most preferably, at 1 phr or less.
  • an antioxidant such as triphosphite antioxidants, hindered phenol antioxidants either alone or in the combination with other antioxidant(s)
  • triphosphite antioxidants are tris(di-tertiary butylphenyl)phosphite, tris-nonylphenylphosphite; and typical examples of the hindered phenol antioxidants are 4,4′-butylidene bis-(3-methyl-6-tert-butylphenol), 2-4-bis[(octylthio)methyl]-o-cresol.
  • thermoplastic elastomer composition is a blend of a halogenated isobutylene elastomer and a polyamide, which is subjected to dynamic vulcanization.
  • dynamic vulcanization is used herein to connote a vulcanization process in which the engineering resin and a vulcanizable elastomer are vulcanized under conditions of high shear. As a result, the vulcanizable elastomer is simultaneously crosslinked and dispersed as fine particles of a “micro gel” within the engineering resin matrix.
  • Dynamic vulcanization is effected by mixing the ingredients at a temperature which is at or above the curing temperature of the elastomer in equipment such as roll mills, Banbury® mixers, continuous mixers, kneaders or mixing extruders, e.g., twin screw extruders.
  • the unique characteristic of the dynamically cured compositions is that, notwithstanding the fact that the elastomer component may be fully cured, the compositions can be processed and reprocessed by conventional thermoplastic resin processing techniques such as extrusion, injection molding, compression molding, etc. Scrap or flashing can be salvaged and reprocessed.
  • the halogenated isobutylene elastomer component include copolymers of isobutylene and para-alkylstyrene, such as described in European Patent Application 0 344 021.
  • the copolymers preferably have a substantially homogeneous compositional distribution.
  • Preferred alkyl groups for the para-alkyl styrene moiety include alkyl groups having from 1 to 5 carbon atoms, primary haloalkyl, secondary haloalkyl having from 1 to 5 carbon atoms and mixtures thereof.
  • a preferred copolymer comprises isobutylene and paramethylstyrene.
  • Suitable halogenated isobutylene elastomer components include copolymers (such as brominated isobutylene-paramethylstyrene copolymers) having a number average molecular weight Mn of at least about 25,000, preferably at least about 50,000, preferably at least about 75,000, preferably at least about 100,000, preferably at least about 150,000.
  • the copolymers may also have a ratio of weight average molecular weight (Mw) to number average molecular weight (Mn), i.e., Mw/Mn of less than about 6, preferably less than about 4, more preferably less than about 2.5, most preferably less than about 2.0.
  • suitable halogenated isobutylene elastomer components include copolymers (such as brominated isobutylene-paramethylstyrene copolymers) having a Mooney viscosity (1+4) at 125° C. (as measured by ASTM D 1646-99) of 25 or more, preferably 30 or more, more preferably 40 or more.
  • Preferred brominated copolymers of isobutylene and paramethylstyrene include those having 5 to 12 weight % paramethylstyrene, 0.3 to 1.8 mol % brominated paramethylstyrene, and a Mooney viscosity of 30 to 65(1+4) at 125° C. (as measured by ASTM D 1646-99).
  • the halogenated isobutylene elastomer component (A) can be prepared from isobutylene and about 0.5 to 25% by weight, preferably about 2 to 20% by weight, based upon the total amount of the comonomers, of p-alkylstyrene, preferably p-methylstyrene, followed by the halogenation.
  • the content of the halogen e.g., Br and/or Cl, preferably Br
  • copolymerization can be carried out in a known manner as described in, for example, European Patent Publication No. EP-34402/A published Nov. 29, 1989 and the halogenation can be carried out in a known method as described in, for example, U.S. Pat. No. 4,548,995.
  • the halogenated isobutylene elastomer preferably has the number-average molecular weight (Mn) of at least about 25,000, more preferably at least about 100,000 and a ratio of the weight-average molecular weight Mw to the number-average molecular weight (Mn), i.e., Mw/Mn of preferably less than about 10, more preferably less than about 8.
  • the polyamides usable in the present invention are thermoplastic polyamides (nylons) comprise crystalline or resinous, high molecular weight solid polymers including copolymers and terpolymers having recurring amide units within the polymer chain.
  • Polyamides may be prepared by polymerization of one or more epsilon lactams such as caprolactam, pyrrolidione, lauryllactam and aminoundecanoic lactam, or amino acid, or by condensation of dibasic acids and diamines. Both fiber-forming and molding grade nylons are suitable.
  • polyamides examples include polycaprolactam (Nylon 6), polylauryllactam (Nylon 12), polyhexamethyleneadipamide (Nylon 66), polyhexamethyleneazelamide (Nylon 69), polyhexamethylenesebacamide (Nylon 610), polyhexamethyleneisophthalamide (Nylon 6 IP) and the condensation product of 11-amino-undecanoic acid (Nylon 11).
  • Nylon 6 (N6), Nylon 11 (N11), Nylon 12 (N12), a Nylon 6/66 copolymer (N6/66), Nylon 610 (N610), Nylon 46, Nylon MXD6, Nylon 69 and Nylon 612 (N612) may also be used.
  • copolymers thereof any blends thereof may also be used. Additional examples of satisfactory polyamides (especially those having a softening point below 275° C.) are described in Kirk-Othmer, Encyclopedia of Chemical Technology, v. 10, page 919, and Encyclopedia of Polymer Science and Technology, Vol. 10, pages 392-414. Commercially available thermoplastic polyamides may be advantageously used in the practice of this invention, with linear crystalline polyamides having a softening point or melting point between 160° C.-230° C. being preferred.
  • the amounts of the elastomer (A) and the polyamide (B) usable in the present invention is preferably 95 to 25 parts by weight and 5 to 75 parts by weight, more preferably 90 to 25 parts by weight and 10 to 75 parts by weight, respectively, provided that the total amount of the components (A) and (B) is 100 parts by weight.
  • the method for producing the thermoplastic elastomer composition in the present invention consists of melting and kneading the halogenated isobutylene elastomer (A), the polyamide (B) and the antioxidant (C) by a biaxial kneader/extruder etc. to disperse the elastomer (A) in the polyamide (B) forming the continuous phase.
  • a vulcanization agent is added, while kneading, and the elastomer component is dynamically vulcanized.
  • the various compounding agents (except vulcanization agent) for the elastomer and the polyamide may be added during the above kneading, but preferably are mixed in advance before the kneading.
  • the kneader used for kneading the polyamide and the elastomer is not particularly limited. Examples thereof are a screw extruder, kneader, banbury mixer, biaxial kneader/extruder, etc. Among these, it is preferable to use a biaxial kneader/extruder for the kneading of the thermoplastic resin and the elastomer and the dynamic vulcanization of the elastomer.
  • two or more types of kneaders may be used for successive kneading.
  • the temperature should be at least the temperature where the polyamide melts.
  • the shear rate at the time of kneading is preferably 500 to 7500 sec ⁇ 1 .
  • the time for the overall kneading is from 30 seconds to 10 minutes.
  • the vulcanization time after addition is preferably 15 seconds to 5 minutes.
  • the elastomer composition produced by the above method is then extruded or calendered into a film.
  • the method of forming the film may be a usual method of forming a film from a thermoplastic resin or thermoplastic elastomer.
  • the elastomer composition according to the present invention may contain, in addition to the above-mentioned essential ingredients, a vulcanization or cross-linking agent, a vulcanization or cross-linking accelerator, various types of oils, an antiaging agent, reinforcing agent, plasticizer, softening agent, or other various additives generally mixed into general rubbers.
  • the compounds are mixed and vulcanized by general methods to make the composition which may then be used for vulcanization or cross-linking.
  • the amounts of these additives added may be made the amounts generally added in the past so long as they do not run counter to the object of the present invention.
  • Example 3 Comparative
  • Exxpro 89.4 was kneaded in a bambury mixer, followed by pelletizing in a conventional manner with coating with the granulator. Thereafter, the resultant pellets and Nylon and the additives shown in Table 1 were dynamically vulcanized by a biaxial extruder at 230° C. and a shear rate of 1000 s ⁇ 1 .
  • the film using the antioxidant as a granulator has good elongation compare to cure agent as a granulator.
  • the film using antioxidant as a granulator has same excellent low temperature durability and low temperature stability as the film using talc.
  • the films having the composition listed in Table 1 were blown using the same blow die.
  • the mechanical properties thereof are listed in Table 3.
  • the mechanical properties of the thermoplastic elastomer containing the rubber particles with improved rubber pelletization process are good.
  • the film has the same mechanical properties.
  • the film using the antioxidant as a granulator has the same elongation as in the case of using talc as a granulator. Also, the film using antioxidant as a granulator has the same excellent low temperature durability.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
US10/548,063 2003-03-06 2003-03-06 Thermoplastic elastomer composition with an improved rubber pelletization process Abandoned US20060252874A1 (en)

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US11/932,651 US20080058472A1 (en) 2003-03-06 2007-10-31 Thermoplastic elastomer composition with an improved rubber pelletization process

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PCT/US2003/006702 WO2004081108A1 (en) 2003-03-06 2003-03-06 Thermoplastic elastomer composition with an improved rubber pelletization process

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US (2) US20060252874A1 (ja)
EP (1) EP1599540B1 (ja)
JP (1) JP4624111B2 (ja)
CN (1) CN100535046C (ja)
AU (1) AU2003216520A1 (ja)
CA (1) CA2518087C (ja)
DE (1) DE60329127D1 (ja)
WO (1) WO2004081108A1 (ja)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010071642A1 (en) * 2008-12-17 2010-06-24 Exxonmobil Chemical Patents, Inc. Stabilized dynamically vulcanized thermoplastic elastomer compositions useful in fluid barrier applications
US8933172B2 (en) 2010-06-25 2015-01-13 The Yokohama Rubber Co., Ltd. Thermoplastic elastomer composition and manufacturing method therefor
US9120927B2 (en) 2010-09-29 2015-09-01 The Yokohama Rubber Co., Ltd. Process for producing thermoplastic elastomer composition
US9884515B2 (en) 2013-02-28 2018-02-06 Bridgestone Corporation Tire

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US20050113532A1 (en) * 2003-11-26 2005-05-26 Fish Robert B.Jr. High flow, toughened, weatherable polyamide compositions containing a blend of stabilizers
JP5328358B2 (ja) 2005-10-27 2013-10-30 エクソンモービル ケミカル パテンツ，インコーポレイティド 低透過性熱可塑性エラストマー組成物
CA2627299C (en) 2005-10-27 2011-12-20 Exxonmobil Chemical Patents Inc. Construction comprising tie layer
EP2502742B1 (en) 2005-10-27 2017-06-21 ExxonMobil Chemical Patents Inc. Construction comprising tie layer for pneumatic tire
RU2406609C2 (ru) 2005-10-27 2010-12-20 Эксонмобил Кемикал Пэйтентс Инк. Конструкция, содержащая соединительный слой
CN101356065B (zh) 2006-01-10 2011-12-14 横滨橡胶株式会社 具有低空气渗透性的热塑性聚合物组合物的层压材料及使用该层压材料作为内衬的充气轮胎
CN101541530B (zh) 2006-10-26 2015-09-09 埃克森美孚化学专利公司 低湿气渗透性层压结构
US8846792B2 (en) 2006-10-26 2014-09-30 The Yokohama Rubber Co., Ltd. Construction comprising tie layer
US8450396B2 (en) 2007-10-11 2013-05-28 Exxonmobil Chemical Patents Inc. Efficient mixing process for producing thermoplastic elastomer composition
EP2209818B1 (en) * 2007-11-14 2011-06-08 ExxonMobil Chemical Patents Inc. Triethylamine functionalized elastomer in barrier applications
US9586355B2 (en) * 2011-03-11 2017-03-07 Exxonmobil Chemical Patents Inc. Dynamically vulcanized thermoplastic elastomer film
US8530581B2 (en) 2011-12-12 2013-09-10 Exxonmobil Chemical Patents Inc. Powder, compositions thereof, processes for making the same, and articles made therefrom
EP2861662B1 (en) * 2012-06-19 2019-09-25 The Yokohama Rubber Co., Ltd. Thermoplastic elastomer composition and process to produce same
JP6238990B2 (ja) 2012-09-06 2017-11-29 エクソンモービル ケミカル パテンツ，インコーポレイティド タイ層を含む構造体
JP5668876B2 (ja) * 2014-02-07 2015-02-12 横浜ゴム株式会社 熱可塑性エラストマー組成物の製造方法

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Publication number Priority date Publication date Assignee Title
WO2010071642A1 (en) * 2008-12-17 2010-06-24 Exxonmobil Chemical Patents, Inc. Stabilized dynamically vulcanized thermoplastic elastomer compositions useful in fluid barrier applications
RU2495064C2 (ru) * 2008-12-17 2013-10-10 Эксонмобил Кемикал Пэйтентс, Инк. Стабилизированные композиции на основе термоэластопласта динамической вулканизации для использования в барьерных изделиях для текучих сред
US9540510B2 (en) 2008-12-17 2017-01-10 The Yokohama Rubber Co., Ltd Stabilized dynamically vulcanized thermoplastic elastomer compositions useful in fluid barrier applications
US8933172B2 (en) 2010-06-25 2015-01-13 The Yokohama Rubber Co., Ltd. Thermoplastic elastomer composition and manufacturing method therefor
US9120927B2 (en) 2010-09-29 2015-09-01 The Yokohama Rubber Co., Ltd. Process for producing thermoplastic elastomer composition
US9884515B2 (en) 2013-02-28 2018-02-06 Bridgestone Corporation Tire

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Publication number Publication date
EP1599540B1 (en) 2009-09-02
AU2003216520A8 (en) 2004-09-30
US20080058472A1 (en) 2008-03-06
DE60329127D1 (de) 2009-10-15
CN1751094A (zh) 2006-03-22
EP1599540A1 (en) 2005-11-30
WO2004081108A1 (en) 2004-09-23
CN100535046C (zh) 2009-09-02
CA2518087A1 (en) 2004-09-23
AU2003216520A1 (en) 2004-09-30
CA2518087C (en) 2010-05-25
JP2006514141A (ja) 2006-04-27
JP4624111B2 (ja) 2011-02-02

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Owner name: EXXONMOBIL CHEMICAL PATENTS, INC., TEXAS

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